


Pretty Boys and Poetry

by Cello_trash



Category: Check Please! (Webcomic)
Genre: Emotional Constipation, Eventual Smut, Fluff, Friends to Lovers, Getting Together, Light Angst, M/M, Trans William "Dex" Poindexter, but they work it out, ftm dex, in the third chapter
Language: English
Status: Completed
Published: 2021-01-11
Updated: 2021-01-14
Packaged: 2021-03-16 00:13:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 6,430
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28697505
Author URL: https://archiveofourown.org/users/Cello_trash/pseuds/Cello_trash
Summary: Dex glared at the computer in front of him, willing his brain to come up with something, anything, to write down, but his mind was completely blank. Taking a poetry class was the dumbest idea he’d ever had. Or, more accurately, the dumbest idea since falling in love with his teammate.AKA Dex secretly loves Nursey's poetry and signs up for a poetry class himself... this leads to feelings, confessions, and eventually a happily ever after
Relationships: Derek "Nursey" Nurse/William "Dex" Poindexter
Comments: 9
Kudos: 66





	1. Chapter 1

Dex glared at the computer in front of him, willing his brain to come up with something, anything, to write down, but his mind was completely blank. Taking a poetry class was the dumbest idea he’d ever had. Or, more accurately, the dumbest idea since falling in love with his teammate.

As if Dex’s thoughts had summoned him, Nursey walked into their shared room in the Haus, “What’s up poindexter?”

Will quickly switched over from his word document to google (not that he’d been able to write a single word). “Just, uh… doing some work for a class, what about you?”

“Oh chill what class?” Nursey leaned against the side of the desk that Dex was sitting at and Dex couldn’t help but be amazed by just how attractive Nursey could be in ratty sweats and a beanie. Anyone else would look like a mess, but Nursey looked radiant, his lips quirked up slightly as he stared down at Will as if he was already brainstorming ways to tease Dex. He probably was. Derek was witty like that and knew just how to rile him up.

They’d moved past their real animosity months ago, and while they still traded insults with each other, they had a playful quality to them instead of the truly hurtful barbs from their first year.

“Ummm this CS class for my major... I’m having trouble with the code; it just won’t work…”

“I’m sure it can’t be that hard,” Nursey responded, “if you show it to me maybe I’ll be able to figure it out for you.”

“Shut the fuck up Nurse,” Dex tried to face wash him, but the angle he had was awkward and he mostly just ineffectually flailed in Nursey’s direction. Nursey laughed and moved to sit on the bottom bunk, pulling out his journal that Dex knew he wrote all of his personal poetry in.

“What are you up to?” Dex asked, although it was clear Nursey was writing.

“I’m performing at a poetry reading tonight at the student union,” Nursey replied, making little edits to what he’d written, “I’m just making the finishing touches to the piece I’m reading tonight.”

Dex would never admit it, but he had already known about the poetry reading. He’d attended the readings for almost 1.5 semesters in order to see Nursey perform in secret, hat pulled down far over his face, standing in the very back of the room by the door, leaving the minute Nursey was done. He would be even less willing to admit that going to see Nursey was the reason why he had registered for this fucking poetry class in the first place in an attempt to understand what Nursey was passionate about, although Dex still didn’t get the appeal of writing his own poetry.

“Okay, well um… let me know how it goes I guess…” Dex said.

After thirty minutes of relative silence, Nursey cleared his throat, “Alright bro, I’m gonna head out,” Nursey stood up and stretched, his shirt riding up his trim waist; Dex couldn’t take his eyes off of the strip of Nursey’s skin that was revealed. He knew that he saw Nursey naked all the time in the locker room, but anytime something like this happened it was more appealing for some reason, it felt like more of a secret. Dex could feel his face flush in embarrassment.

“You good Dexy, you look like a lobster?”

“Shut up,” Dex grumbled.

“Aww don’t be like that, you look like a very sexy lobster,” Nursey chirped as he walked out the door. Dex watched him go and then dropped his head on his desk. He needed to get over Nursey, this was getting ridiculous. Turning back to his computer, Dex went back to staring at his blank word document and sighed. He had two hours before he needed to leave for Nursey’s open mic night.

Dex slipped into the room where the mic night was held, squeezing between several people, breathing hard. He had lost track of time and had to run to the union to make it on time. The first person had already started their piece, but Dex really only cared about making it in time for Nursey. Several of the participants’ pieces were interesting to Dex, but he knew that Nursey would blow everyone else out of the water. Maybe he was just biased.

Finally, Nursey walked up to the stage in tight black jeans, a shirt that showed off his broad shoulders, and a beanie. Dex always teased him for looking like a hipster, but he secretly found Nursey’s outfits very attractive. Nursey cleared his throat and the room fell silent; Dex wasn’t the only one eagerly waiting for Nursey’s turn. Right as he opened his mouth, Nursey scanned the crowd and clearly noticed Dex, locking eyes with him. While normally Nursey would shift his eyes around the crowd, tonight he never broke eye contact with Dex. Something about Nursey’s gaze made every word he spoke more intimate and intense, and Dex couldn’t make himself look away either. Once Nursey was done, and the snaps and applause had calmed down, he made a beeline towards Dex.

“Hey dude, what are you doing here?” Nursey asked once he was in earshot. Dex laughed awkwardly.

“You mentioned this was happening and I just uh, wanted to come to see you, you know bros support bros,” Dex mumbled. Nursey’s face lit up, “Cool… I’ve seen everyone I wanted to perform so do you maybe want to get out of here and hang at the Haus? I got your favorite ice cream from the store the other day, we could watch a cheesy movie and eat ice cream straight out of the carton.”

Dex shoved Nursey, “you’re a heathen you know that?” He then added quietly, “but I’d love all of that…”

Nursey laughed as the two of them headed towards the door, “Don’t try to act like you aren’t as gross Dexy.”  
As they were walking back to the Haus in the dark, Dex kept shooting glances over at Nursey. Finally he said, “You were really good up there tonight…” and then immediately blushed.

“Thanks, that means a lot,” Nursey replied, and Dex was taken aback by how serious and sincere Nursey sounded. Nursey always seemed to have a nonchalant, joking attitude, and Dex wasn’t sure if he’d ever seen Nursey like this when he wasn’t performing.

Dex suddenly blurted out, “I’m actually taking a poetry class this semester and you definitely inspired me, so… yeah…” he trailed off awkwardly, mentally facepalming. How did he always manage to make things weird when it was just he and Nursey. It was like his social skills flew out the window whenever the other boy was around. Dex's brain, in Nursey's voice, piped up, _'you don't have any social skills in the first place poindexter.'_ Dex smiled secretly to himself.

“Bro! Why didn’t you tell me earlier, it’s almost the end of the semester, you’ve been holding out on me!” Nursey yelled exuberantly. Nursey was practically vibrating with excitement, “can I see some of your poetry… bro we can like, exchange poetry and proofread each other’s stuff… BRO.”

Dex was about to agree; he DID need help with his poetry and having Nursey read over it would absolutely help, but then he remembered the contents of his best poetry: Nursey’s green eyes, his strong, yet gentle hands, his smirks and smiles, Dex’s own relationship with his body, his discomfort.

Dex fiddled with his sleeves, “Umm, maybe sometime… I don’t really know about that…”

“Ahhh, come on it can’t be that bad,” Nursey whined, “I want to see what my amazing D-man partner writes about, what sparks his imagination.”

Dex started to panic slightly, throwing up his defensive walls, “I said no, Derek.”

Nursey seemed shocked at the use of his first name. “I didn’t mean to make you upset Will… you don’t have to show me anything you don’t want to, but if you change your mind I’m interested okay?”

Dex glanced over to Nursey and gave him a small, genuine smile as he opened the door to the Haus, “Alright, I’ll let you know.”


	2. Chapter 2

**Notes for the Chapter:**

> This ended up being longer than I thought it was going to be, so I split it up into 3 chapters instead of 2; the last chapter should still be out sometime today tho :)

Nursey knew that he shouldn’t be snooping in Dex’s stuff like this, but he really wanted to read some of Dex’s poetry. Dex was self-conscious about everything when he had no reason to be, and Nursey wanted to prove that to Dex by telling him his poetry was good. Nursey looked over his shoulder as he started to file through Dex’s bookbag. Ah hah! Nursey thought as he found a notebook, and when he opened it up, there was Dex’s handwriting scrawled across the pages.

Nursey smiled as he started to read. It wasn’t especially polished, but it was clear that Dex had a big crush on someone. Nursey’s eyebrows raised as he realized that it was a male someone. He knew at this point that he had majorly invaded Dex’s privacy; Dex hadn’t come out to any of them yet, and it was an asshole move that Nursey was finding out like this without his permission, but he was too curious to stop. It’s not like he’d confront Will about it anyway. His smile started to fade into surprise and regret as he noticed something about the boy that Dex was writing about. Maybe it was wishful thinking or vanity, but Nursey could have sworn Dex was talking about HIM. His suspicions were quickly confirmed when Dex started writing about his skating.

Nursey slammed the notebook shut, shoving it back into Dex’s bag, feeling guilty. It wasn’t like he was upset about Dex’s interest in him, in fact it was quite the opposite, but Nursey felt dirty for finding out in this way. He had gone too far. 

Trying to pull himself out of a guilt spiral, Nursery had a thought. There was one way to make this up to Dex: let Dex know he was interested in him as well. Nursey’s resolve hardened; he’d be Dex’s boyfriend by the end of the semester if it killed him.

Of course that was easier said than done. Nursey was flirting as hard as he could, telling Dex that he looked hot or complimenting his skating or his baking skills or offering to help Will when he was doing repairs around the Haus, but Dex would just turn bright red and run away. For god’s sake Nursey had even told Dex he had a cute butt the other day and the redhead had just looked at him like he was an idiot before scuttling off to the library. There was only so far Nursey could debase himself in an attempt to get Will to flirt back. If it weren’t for Dex’s adorable full body blush, Nursey would have thought that he must have hallucinated reading Dex’s poetry for how the other boy was blowing him off at every advance.

He was saying as much on a facetime with his moms, when they both broke out into laughter. “You could always just directly ask him out instead of flirting with him, hoping he’ll catch the signals you’re putting out,” his mom chuckled. Nursey balked at the idea.

“If I did that Dex would just shutdown and run away and we’d just go back to how things were are first year,” Nursey said defensively.

His mama snorted, “Don’t try to sell us that bullshit Derek Malik Nurse, you’re just scared of rejection.” When Nursey opened his mouth to object, she continued, “And I don’t even know why you’re scared, you already know he likes you.” While he was reticent to admit it, Nursey knew that calling his moms would be a good idea. They had an ability to call him out when he was being stupid. Now he was reinvigorated, and a new plan. There was a house party this weekend, and he knew that Dex was on Nursey patrol… he’d make his move there.

Something was up with Nursey, but he couldn’t tell what, so Dex was on edge. Normally by this time, Nursey would already be plastered and trying to dance naked on the table, but he was cold sober. Nursey had been acting weird the past several weeks, and if Dex didn’t know better he’d say that Nursey had been flirting with him. But that couldn’t be possible, Nursey thought he was a homophobic republican. Plus Nursey was so far out of Dex’s league it wasn’t even funny. So there was no way that Nursey might be attracted to him.

“Come on Dex, dance with me!” Nursey grabbed Dex’s arm, pulling him towards the center of the room where people were grinding up against each other.

“I don’t know about this Nurse…” Dex tried to pull them back to the edges of the room, “I’m not a good dancer…”

Nursey turned and shot him a blinding smile that had Dex docilely following behind, “You don’t have to be skilled at dancing to be good at dancing, you just have to commit to it!” Nursey yelled over the loud music. 

Dex begrudgingly followed Nursey onto the dance floor and Nursey immediately plastered himself to Dex’s back, dancing up on him. Dex tried to ignore it; Nursey was often touchy feely at parties, but he hadn’t had a single drink tonight. Dex felt Nursey’s hands on his hips and all of a sudden a burst of bravery shot through him. “What are you doing?” he asked, turning so that he and Nursey were face to face.

Nursey gave him another big smile, “I’m trying to woo you Poindex.” Will’s brain came to a sudden halt and he felt slightly lightheaded. 

“Can you repeat that?” He asked weakly. Nursey nodded agreeably, “I’m trying to woo you, ask you out, go steady with me, all that jazz.”

Dex knew that his face was beet red. He pinched himself to make sure he wasn’t dreaming and Nursey laughed. Dex was suddenly aware of all the people surrounding them. “Can we go somewhere else a little more private to talk about this?” the redhead asked.

“Of course sexy Dexy,” Nursey smirked. The two boys made their way through the crowd towards the stairs, ducking under the police tape at the top of the stairs, and jogged to their room. Once inside Dex pushed Nursey into the door, kissing him roughly. Less than an hour ago, he thought he had absolutely no chance with Nursey, but now that Nursey liked him, he couldn’t hold back anymore. Their noses bumped against each other when they didn’t quite get the angle right and their teeth clashed at the jarring sensation of slamming into the door. It was by no means a graceful kiss, but Dex didn’t have much experience to compare it with anyways, and the fact that it was Nursey, still had Dex moaning into Nursey’s mouth. Hopefully they’d have plenty of time to practice kissing.

“Will,” Nursey gasped. 

Dex groaned, murmuring, “I like it when you call me Will.” Nursey smirked, “Noted.” And then dove back in to kiss Dex. Everything was very much going well, when Nursey went to grind into Will. Derek looked at him confused when he didn’t feel anything, “Are you not enjoying this bro?”

Will looked away, embarrassed, finding it a little hard to breathe. He wasn’t sure why he hadn’t thought of this issue before he started kissing Nursey. Finally he said, “First of all don’t fucking call me bro after shittily asking me out.”

Nursey let out an indignant squawk, “It was a romantic ‘bro.’”

“And second of all, uh… I’m trans and I really like you, but I’m pre-op on top and I don’t plan on ever having bottom surgery and so I understand if this is a dealbreaker for you so yeah…” Dex looked up at Nursey to find him looking horrified. Dex could feel the tears building up behind his eyes… Was he really that gross? But when Nursey opened his mouth, the taller boy said something Dex would’ve never thought of.

“Dex! Have you been working out and playing games with a binder on??” Nursey seemed quite upset at the idea. It took several seconds for Dex’s brain to truly comprehend what Nursey had said.

“Well, I mean I know I’m not supposed to but… like I really can’t leave the house without it on, so it’s a lesser of two evils thing…” Dex mumbled. 

Nursey looked like he was about to argue, but stopped himself, looking thoughtful. “I’m not happy about it, but it makes sense… just please tell me if it gets too bad, and like…” A look of understanding washed over his face, “Wait! That’s why you always wait for everyone else to leave to shower and you bundle up in your blankets the moment you get undressed… Dex you have to be wearing that thing for like at least like 16 hours everyday.” Nursey grabbed Dex by the shoulders and looked deep into his eyes. “From now on please at least take you binder off when it’s just the two of us in this room please I hate the idea that you might be permanently hurting yourself,” Nursey pleaded. 

Dex bit his lip nervously, shifting slightly side to side, “I uh…. I can’t promise you anything but I’ll try ok… I’ll try…”

Nursey smiled at him, “That’s all I can ask really.”

“Is that really what was the thing you latched onto? That I’m binding more than I should, and not the whole I don’t have a dick thing??” Dex asked, baffled. 

When Nursey just continued to smile kindly at Dex, he bit into his lip harder before opening his mouth, “So I uh… I appreciate you being chill about this but um… would you want to be together or no, like knowing I’m trans as a friend is a lot different than knowing I’m trans as a partner so yeah, just like what are you going to do-”

Dex was cut off by Nursey kissing him. He hadn’t been able to look at Nursey, and so even though Nursey’s kiss wasn’t aggressive, Dex hadn’t seen it coming, letting out a squeak as their lips collided awkwardly. 

“It doesn’t change anything Will,” Nursey pressed his forehead against Dex’s, “I am still just as crazy about you as I was ten minutes ago.” Dex couldn’t have stopped the wide grin from stretching across his face even if he wanted to. 

“Now where were we?” Nursey winked at him before sucking a hickey into Will’s neck. “Wait,” Dex gasped out, “I know I was the one to start this, but all I’ve done is kiss a few people and I’ve never gone further and I don’t really think I want to tonight.”

“Has anyone else ever told you that you’re adorable when blush,” Nursey said, but his tone wasn’t joking, it was serious. Nevertheless, Derek led them towards the bottom bunk, “Do you feel comfortable laying down with me?” Derek asked. At Dex’s apprehensive look, he assured, “I’m not gonna do anything you don’t want me to, I’d just like to snuggle if you’re okay with that…”

Dex nodded shyly, “Can you turn around while I take my binder off?”

“Pinkie promise I won’t turn around and look,” Nursey literally held out his pinkie. Dex hooked their pinkies together and gave Derek’s a squeeze before dropping his hand and spinning Nursey around. He could hear Nursey laying down in bed.

The minute Dex had his binder off, he vaulted into the bottom bunk, burrowing his face into the crook of Nursey’s neck. He could feel the vibrations of Derek laughing sweetly. Eventually Dex pulled back slightly in order to look at Nursey, “Do you think this will actually work?” Dex’s voice sounded a lot smaller than he’d meant it to, “We’re always fighting, and once the happiness of a new relationship wears off, do you think we’ll be able to resist tearing each other apart?”

Nursey looked at Dex like he was just a little bit stupid, “I don’t think our ‘arguements’ have been meanspirited in a long time, Will… I mean obviously we still have some real arguments, but as long as we communicate, I don’t see it being a problem.”

Dex huffed, “Yeah because we both know that communication is my biggest strong suit,” his eyebrows furrowed in frustration at himself and his inability to talk about his feelings.

Nursey nodded his head thoughtfully, “Yeah, well that’s something we can work on together, huh?”

Dex gave Nursey a quiet smile, “Yeah I guess…” 

Neither of them said anything for several minutes until Nursey started to speak, “As long as we’re communicating with each other, I have something to confess…” Dex tensed up. “I may have snuck in here a couple weeks ago and found your poetry and read some of it… I stopped as soon as I realized you had a crush on me, but yeah… sorry about invading your privacy like that…” 

Derek was nervous that Will was going to blow up at him, but all the redhead did was grumble and twist Nursey’s nipple hard, “Jerk, I knew you weren’t brave enough to be so bold as to just ask me out on the dance floor.”

“Hey!” Nursey shouted in indignation, “How dare you say things about me that are complete correct!” The two chuckled. As much as he knew he needed to work on it, Dex also knew that he was done with communicating feelings for today, “Can we just snuggle right now?”

Nursey laughed again, “Of course, snuggles now, talking later.” Nursey gave Dex one last kiss before gathering Dex up in his arms.


	3. Chapter 3

**Notes for the Chapter:**

> This is my first time writing smut so let me know whether it's super bad or not lol... I tried to write it in a more realistic way for someone's first time (i.e. it's pretty awkward y'all)/ include the conversations you should have before/during you have sex with anyone (but esp trans people) about how and where they want to be touched.

They had just come back from a date walking around the pond where they had bought ice cream and sat on a park bench, discreetly holding hands. Nursey had reassured Dex that he wasn’t upset that Dex wasn’t ready for anyone to know yet, but Dex still felt guilty about making Derek hide their relationship. “Come out when you’re ready… come out for YOU, Dex, don’t come out for me,” Nursey had said on their first date when Dex had expressed his guilt to Nursey. Derek had also given him a kiss for being open with him about his concerns; Nursey had decided that bribing Will with kisses in order to get him to open up was a good strategy (Dex wouldn’t ever admit it, but it did work).

They were now both sitting on the bottom bunk making out. They had made out several times since the party, but before things could get really heavy Dex had always backed out, not comfortable yet with Derek seeing him naked. This time though, Dex felt ready. He wanted to go farther. He pressed further into the kiss, deeping it, and pushed Nursey down until the taller boy was laying flat on his back. Nursey raised an eyebrow in a silent question. Dex didn’t feel like talking, so he straddled Nursey, settling right above Nursey’s crotch, not quite sure how to position his body in a way that wasn’t awkward. After a few seconds, Nursey broke away, putting a hand on Dex’s chest when he tried to go back in for another kiss.

“Wait, Dex… I think I’m at the point where we need to stop, this is getting a bit too intense,” Nursey panted. 

Dex shook his head violently, “I’m ready, I want to do this.” He tried to lean back down, and was surprised when Derek’s palm was still firmly pushing him backwards. Nursey sat up slightly, maneuvering them until they were both crossed legged, staring at each other. 

“I’m not going any further until we have a conversation about what you need from me.” Dex pouted, but Nursey didn’t budge. “I need to know what you want me to call shit and where I can and can’t touch and how I can touch… I don’t want to trigger you Will, and I know it’s uncomfortable but I need this information before I’m willing to do anything more than making out.”

Dex hid his face in Nursey’s chest, “Um… word wise, I call it my chest, not my ti-, you know what I’m talking about, and I have a dick, not a, you know…and I don’t have a pussy… you can touch it, but I’d prefer if you just sort of didn’t refer to it as anything.”

“Sounds like a plan,” Nursey said quietly, and Dex liked how he could feel Derek’s chest rumble when he spoke this close up. “What else…?”

Dex shook his head, “I’ve never gone farther than this Nurse, I honestly don’t really know yet what will trigger me or not with another person…”

Nursey hummed thoughtfully, “That’s fair… have you ever heard of the stoplight system?”

Dex pulled back, looking slightly alarmed, “umm yes?? But what the fuck are you planning on doing? I don’t think I’m ready to do anything, like… kinky my first time…”

“Nah chill, I don’t plan on doing anything crazy, I just think it might be helpful since we’re walking into this essentially blind… if I do something that doesn’t feel quite right you can call yellow, and if I do something that’s a hard stop you can call red.” Nursey paused, “I’ll feel better about this if I know that you have an easy way of telling me if I mess up.”

“Okay.” Dex thought it made perfect sense. With that, Derek scooted them so that he was kneeling in front of Dex on the bed. 

Nursey gently ran his hands down Will’s arms, until they rested at his waist. When Will nodded, Nursey began to lift Dex’s shirt off. Will expected him to immediately take off his binder as well, but Derek started kissing his neck, working his way downwards, past his collarbones until he was nipping at the little bit of cleavage that was accessible with his binder still his place. Dex tensed slightly, but didn’t want Nursey to stop. 

“Fuck, Derek… please take my binder off, come on… please, I want more… green please green,” Dex murmured as Nursey spent what felt like hours just leaving little bite marks across Will’s upper chest, careful not to leave any above the collar line. Finally, Nursey helped Dex out of the binder, and Dex instinctually covered his chest with his hands, curling into himself. Derek made a quiet, reassuring, cooing noise and moved to grab Dex’s wrists, going slowly so as to give Will time to move or call yellow. When Dex didn’t say anything, Nursey tenderly, yet firmly, moved Dex’s arms away from his body, revealing himself. Dex shivered as Nursey looked at him.

Nursey’s pupils were noticeably dilated, “Will…” he murmured, “god you’re beautiful…” 

Dex immediately tensed, “Yellow.” When Derek backed off, he explained, “That word is traditionally feminine and it just makes me feel feminine and dysphoric is all, we don’t need to stop.” 

“Okay… makes sense… what if I told you that you were really hot and sexy and handsome.”

Dex blushed, feeling slightly hot and bothered, “Yeah that works…” he breathed out.

“Perfect,” Nursey declared, proceeding to push Dex down so that he was flat on his back in the center of the bed, pulling off the redheads pants off and then pulling his own shirt and pants off so they each were down to their underwear. “Is it okay if I suck your dick?” Nursey asked. Will nodded his head, “Fuck, Nursey, you can’t just say shit like that.”

Nursey smirked, before reminding Dex, “Remember, call yellow or red if you need too.” He then leaned down, never breaking eye contact with Dex, as he licked up Dex’s dick before taking it into his mouth, circling his tongue around the tip. Dex had meant to make a snarky remark at Nursey’s comment, but when Nursey wrapped his lips around him, all Dex could let out was a groan. He immediately brought one hand up to cover his mouth to try and be more quiet, and the other carded lightly through Nursey’s hair, trying his hardest not to pull Nursey in closer.

Dex could tell he was just babbling nonsense at this point, a string of ‘dereks’ and ‘pleases’ and ‘oh gods,’ thrusting up into Nursey’s mouth as far as he could. At one point Derek held his hips down with one hand in order to get a better rhythm going, and Dex couldn’t decide whether he was annoyed because he didn’t have control in that moment or turned on by how easily Nursey could pin him down. He whined when Derek pulled away.

“How far do you want this to go, Dex? Like do you just want to stick to external stuff or what?”

Dex took a minute to really think about it. “I think I want you to fuck me Derek… and like, if you don’t mind can it be… here…?” Dex asked, guiding Nursey’s hand to his front hole to indicate what he was talking about, “I don’t think I’d mind anal, I just… like I haven’t done any prep or anything and I’d just be nervous the entire time that I wasn’t clean enough, but if you don’t want to we can maybe do anal or just not fuck yet or something.”

“Course it’s okay Will, just let me get up and get a condom alright…” Dex watched as Derek rifled through his top drawer.

“Can you also get some lube… I still produce some natural lube, but T lessens how much, so we’ll need that to make it comfortable…”

“Sure,” Nursey grabbed a packet and knee walked back over so he was in front of Will, throwing the condom aside for a minute before lubing up several of his fingers. He moved to kiss Will deeply, distracting him as he circled his finger around his entrance, “Relax for me,” he whispered into Will’s mouth, and Will realized he had unconsciously tensed up. When he made an effort to relax, Nursey smiled, nipping and sucking at Dex’s neck as he pushed his first finger in. Dex clenched down hard and Nursey asked, “What’s your color?”

“Green,” Will responded, “It’s just weird right now, I’ll let you know if it gets bad.” Derek hummed, waiting for Dex to relax again before he started moving his finger in and out, wigging it slightly side to side to try and stretch the muscles. Right before he pushed a second finger in he went down on Will again. The penetration itself still wasn’t really pleasurable to Will, but he was now squirming, “More, please give me more Derek.” Nursey scissored his fingers, and when Dex felt Nursey’s tongue at his entrance he gasped, “Wait you don’t have to do that if it tastes weird.”

Derek’s voice was muffled from in between his legs, “You taste fine Will, just try and relax and let me take care of you.” At that Dex realized something.

“Wait, I want to take care of you too,” Dex gasped, but Nursey just shushed him, “That’ll come later, I’m enjoying myself fine just fine right now.” As he was saying that, Dex felt Nursey’s fingers brush a spot inside him that filled him with pleasure, “Holy shit,” he cried out as Derek rubbed at the same spot repeatedly, continuing to open Will up.

By the time Nursey had decided that Will was ready, he had been begging Nursey for what seemed like forever. He watched, panting so hard that he didn’t think he could speak, as Nursey rolled on the condom. 

Dex grunted as Nursey pushed into him. It was back to being uncomfortable, bordering on slightly painful. Nursey skated his hands lightly up and down Will’s sides, murmuring nonsense praise about how good Will was doing, not moving until Will had adjusted to the feeling. Eventually, Derek started to move slowly. When he was able to hit that bundle of nerves inside him, it was pleasant, and the longer Nursey was inside him, the more he relaxed, and the less uncomfortable it was. However, the overwhelming feeling was still that it felt odd, and the vast majority of the pleasure that Dex was feeling was from his own hand circling his dick.

By the time Nursey came, Dex was finally starting to enjoy the feeling of Derek inside him, but nowhere near enough to have come himself yet. “Sorry,” he mumbled as Nursey pulled out and threw the condom away, “You did fine, it just felt weird… give me a second and I’ll be done…” Derek swatted his hand away from his dick and replaced it with his own. 

“Chill, there’s no reason to apologize Dex, first time’s always awkward, there’s nothing to be ashamed of or anything, you’re not gonna hurt my feelings.”

As Nursey started to suck his dick again, Dex reached up to play with his nipples, circling them lightly at first before pinching them, rolling them between his fingers. It didn’t take much longer before Dex felt that telltale tightening feeling in the bottom of his stomach, and he was coming. He bucked, but Nursey kept sucking him off; Will didn’t think he’d had an orgasm that lasted this long ever, but eventually he got oversensitive, whining as he pushed Nursey’s head off of him.

Nursey climbed up the bed so that he and Dex were laying next to each other. After a couple minutes, Dex flicked Nursey, “I can’t believe you told me to ‘chill’ during sex.”

Nursey laughed, before becoming a bit more serious, “I hope that was at least okay for you…”

Dex flicked Nursey again, “It was good, I swear… I’m sure it’ll get better over time. Practice makes perfect after all.” Both boys were smiling goofily at each other, and at Will’s words, Nursey started to smirk.

“Mmmm, when do you think we’ll be able to practice more huh?” Dex rolled his eyes, and moved so that he was octopus hugging Derek, quickly falling asleep.

...

“Oh my goodness, I’m so sorry, sorry I’ll leave!” Dex and Nursey woke up to the sound of Chowder apologizing, backing out of the room and closing the door behind him.

“Shit!” Dex cursed, jumping out of bed, pulling on a pair of boxers and a shirt before starting to pace back and forth. Nursey watched him nervously from the bed. It took 30 minutes before Dex stopped muttering to himself as he paced and returned to sit on the edge of the bed, looking back at Nursey.

“Well… I guess it’s time to start coming out,” the redhead said thoughtfully.

“I’m sure Chowder won’t tell anyone if you’re not ready yet…” Derek offered, but Will just shook his head.

“Nah… if there’s any group of people who won’t care, it’s the team… and I do honestly want to start telling people.” Nursey squeezed Dex’s right hand reassuringly. “And I don’t just mean about our relationship… I want to tell them that I’m trans… having to retcon all of my childhood stories to pretend like I’m cis gets really tiring after a while.”

“As long as you’re comfortable with them knowing, I think that would be a great idea,” Nursey said. “Do you want to do it one-on-one or all at once?”

“I’ll tell Bitty, and then announce it after practice today… rip the bandaid off as it were.”

“Sounds like a plan… and remember that you won’t be alone, I’m with you every step of the way.”

Coming out to the team went as smoothly as they expected. After the initial shock everyone congratulated them, and assured Will that they were there for him in any way he needed.

As they moved closer and closer to the playoffs, Dex let Nursey read more and more of his poetry, getting tips. Will also read Derek’s poetry, but he felt like he never had any helpful advice or criticisms of his boyfriend’s work. He had also started hanging out with more of Nursey’s friends outside of hockey, and while he was often lost when they talked about theory and analyzing prose, he found it enjoyable.

They had a couple of legitimate fights, but each time Will opened up more, communicating earlier, until Will started to share more concerns and insecurities before the fights even happened.

Dex had decided that since Nursey was teaching him about writing, that he’d teach Nursey about baking. They were currently in the kitchen, Dex trying to teach Nursey how to make a pie lattice, laughing at Nursey’s deformed attempts, when Dex felt his phone buzz. Wiping his hands off on his apron, he inhaled sharply when he realized what the email was about. 

Sensing the sudden change of mood, Nursey looked over concerned, “Is everything okay babe?”

“My… uh, my poetry prof just emailed out my grade on my final,” Dex said, panicked, as he quickly unlocked his phone and opened his email, “Holy shit…” he muttered upon scanning the contents of the email, and Nursey looked over his shoulder, dropping a kiss on the back of Dex’s neck when he saw what was written.

“I told you it was really good,” Nursey whispered in Will’s ear, “Congrats on the A… does this mean I can convince you into taking another poetry class next semester?”

Dex snorted as he shook his head, and when he looked at Derek, flour in his dark hair and his nose, he had no choice but to lean in for a kiss. “I’ll leave poetry up to my very talented and smart boyfriend.”

Nursey hummed into the kiss, “Just because writing isn’t your jam doesn’t make you any less talented or intelligent,” he said once they pulled away. 

Dex blushed, “I love you, you know that right?”

“Yeah,” Nursey gave him a big grin, “Love you too.” They embraced again, Dex pushing Nursey back into the counter in a deep kiss as they heard someone from the other room yell, “FINE! THAT’S TOTALLY A FINE!” at them.

Will laughed freely. “We better continue on this pie if we don’t want Bitty to yell at us for defiling his kitchen.”

Derek chuckled before overdramatically snapping to attention, “Yes chef, whatever you say chef.” 

Dex just rolled his eyes and flicked more flour at Nursey before turning back to the pathetic lattice in front of him, wondering how he’d ever fallen for such a dork. It didn’t matter though… he loved his life and for the first time ever, he felt completely free.

**Notes for the Chapter:**

> Thx for reading and plz leave a comment and/or kudos letting me know what you thought of the story :)

**Author's Note:**

> If you liked this leave a kudos and/or comments-- they are the wind beneath my wings, the sustenance I live on, and the air I breathe lol :)  
> The second part of this should be up soon and thx for reading!


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